Within the same region
Anguilla vs Grenada & the Grenadines
Two distinct sailing grounds — here's how they compare on conditions, cost, season, and who they suit.
Quick Comparison
| Dimension | Anguilla | Grenada & the Grenadines |
|---|---|---|
| Region | Caribbean | Caribbean |
| Peak season | Dec, Jan, Feb, Mar, Apr | Dec, Jan, Feb, Mar, Apr |
| Shoulder | Nov, May | Nov, May |
| Sailing difficulty | easy to moderate | moderate |
| Recommended level | beginner friendly | intermediate |
| Avg wind (winter / summer) | 17 / 13 kn | 20 / 15 kn |
| Hurricane risk | Aug, Sep, Oct | Aug, Sep, Oct |
| Currency | XCD (pegged to USD) | XCD (pegged to USD) |
| Mid-tier price (7 days) | $11,500 | $10,500 |
| Luxury tier price | $45,000 | $40,000 |
| Detail page | View → | View → |
At a Glance
Quiet, family-friendly. Often skipped by American bareboat fleet who focus on BVI. Short hop from St Martin (5nm).
- • 2 base marinas
- • 4 must-visit anchorages
- • 31 boats in our fleet database for this region
Stronger trade winds than Northern Caribbean; typically 18-25kt in winter. Tobago Cays is the must-do sail. One-way Grenada to St Lucia possible.
- • 3 base marinas
- • 4 must-visit anchorages
- • 31 boats in our fleet database for this region
Sailing Conditions
Anguilla averages 17 knots in winter and 13 knots in summer. Hurricane risk runs Aug, Sep, Oct — outside these months the sailing is generally dependable.
Grenada & the Grenadines averages 20 knots in winter and 15 knots in summer. Hurricane risk: Aug, Sep, Oct.
In terms of sailing difficulty, Anguilla is generally rated easy to moderate and Grenada & the Grenadines is moderate. The difference matters: Grenada & the Grenadines asks more of the skipper — confidence at the helm and some experience with coastal navigation helps.
Cost Comparison
For a 7-day charter of a typical 45-ft catamaran (4 cabins, sleeps 8):
- Low season: $4,500
- Mid season: $11,500
- High season: $22,000
- Luxury / crewed peak: $45,000+
- Low season: $4,000
- Mid season: $10,500
- High season: $20,000
- Luxury / crewed peak: $40,000+
Bareboat base rates. Crewed typically adds ~$1,500/day (captain + hostess). Prices exclude fuel, provisioning, mooring fees, gratuity.
Anchorages & Must-Do
- Shoal Bay — Often voted world's best beach
- Mead's Bay — Calm; long beach
- Prickly Pear Cays — Day trip; BBQ lunch
- Rendezvous Bay — Anchorage; mellow
- Tobago Cays — Five uninhabited islands; turtle snorkeling
- Petit St Vincent — Quiet luxury island
- Mayreau — Saltwhistle Bay
- Bequia - Friendship Bay — Local charm
Which Should You Choose?
Choose Anguilla. It's the more forgiving first-charter ground — charter fleets are abundant, marina staff speak English, checkout sails are standard.
Both sit in warm waters — temperature is broadly similar. The differentiator is which coast or chain: Anguilla vs Grenada & the Grenadines. Read the must-visit lists above.
Anguilla has 0 cultural anchorages vs Grenada & the Grenadines's 1. Pick by what kind of stop you want between swims.
Timing and Budget: Anguilla vs Grenada & the Grenadines
Frequently Asked Questions
Is Anguilla or Grenada & the Grenadines better for a first-time charter? ▾
Which is cheaper to charter — Anguilla or Grenada & the Grenadines? ▾
When is the best time to visit Anguilla vs Grenada & the Grenadines? ▾
How do sailing conditions compare — Anguilla vs Grenada & the Grenadines? ▾
Which has better flight access — Anguilla or Grenada & the Grenadines? ▾
Which is more beginner-friendly, Anguilla or Grenada & the Grenadines? ▾
Choose Between Anguilla & Grenada & the Grenadines
Tell us your dates and group. We'll recommend the right one — honestly.